The present invention relates to an improved process for preparing phenyl esters of the general formula (I): ##STR1## More particularly, the present invention relates to an improved process for preparing phenyl esters of alkanoyloxyacetic acids in which a salt of a carboxylic acid is reacted with phenyl chloroacetate (II): ##STR2##
The subject phenyl esters of formula (I) are described in U.S. Pat. No. 4,778,618 and are useful as bleach activators. They are conventionally prepared from the corresponding acyloxyacetic acids using methods which are described in U.S. Pat. No. 4,778,618.
In U.S. Pat. No. 4,778,618, Fong et al. describe the following synthesis of alkyl esters of acyloxyacetic acids and references U.S. Pat. 2,659,697, U.S. Pat. No. 2,350,964 and The Journal of the American Chemical Society, 1952, Vol. 74, 3935-3936. ##STR3## Other examples in U.S. Pat. No. 4,778,618 demonstrate that acyloxyacetic acids (III) may be synthesized by the following alternate route: ##STR4##
Thus, known processes requires three or more steps to prepare a phenyl ester of formula (I); they proceed via a substituted acetic acid and they require the preparation of at least one acid chloride.
U.S Pat. Nos. 3,984,454 and 4,154,953 disclose a method for preparing prostanoic acid esters of the formula EQU PG--CH.sub.2 X--Y
wherein PG is the prostanoyloxy radical of a prostaglandin, X is a carbon-carbon single bond, carbonyl or carbonyloxy, and Y is substituted phenyl. By the disclosed method, the unesterfied prostaglandin is reacted, in the presence of an agent which splits off halogen halide, with a compound of the formula Hal--CH.sub.2 --X--Y wherein Hal is a halogen atom, preferably bromine, and X and Y have the values given above. Although starting prostaglandins are all characterized by possessing a esterfiable -COOH group, no other acids are disclosed as undergoing the reaction.
Roczniki Chemii, 1967, Vol 41, 1915-1920 describes the reaction of 4-nitrophenyl bromoacetate with N-protected amino acids to give depsipeptides of glycolic acid. This reaction was not reported with the less expensive and less reactive chloroacetate, with esters derived from phenols other than nitrophenol or with acids other than amino acids.
EP Patent 179,023 describes the reaction of phenyl bromoacetate with polyglutamic acid to give the corresponding phenyloxycarbonylmethyl esters.
GB Patent 1,209,631 describes the reaction of certain phenyl chloroacetates with 4-(1-pyrazolinyl)benzoates to give phenyl esters of benzoyloxyacetic acids. These compounds are claimed as fluorescent whitening agents. The reaction of 1-(4'-carboxyphenyl)-3-(4"-chlorophenyl)-2-pyrazoline with phenyl chloroacetate in the presence of triethylamine is specifically disclosed. The reaction of phenyl chloroacetate with carboxylic acids other than the subject 1-(4'-carboxyphenyl)-3-(substituted phenyl)-2-pyrazolines (i.e., fatty acids) is not reported.
U.S. Pat. No. 4,600,783 describes the reaction of salts of indometacin with tert-butyl chloroacetate in the presence of an inert organic solvent and a phase transfer catalyst. The use of phenyl chloroacetate (II) or of fatty acids in this process is not reported.
U.S. Pat. No. 4,985,180 describes the reaction of salts of 4-(chloroacetyloxy) benzenesulfonic acid and alkanoic acids to give alkanoyloxyacetyloxybenzenesulfonate salts.